Over the past few decades, tourism has come to be considered a way of promoting economic and social development in peripheral, rural areas where traditional agriculture has declined. This is the case of the Portuguese region of Serra da Estrela, where rural tourism has been seen as a strategy for regional development. However, it is important to understand the extent to which tourism activities are able to meet the expectations of tourists and entrepreneurs, in order to represent a realistic development strategy. The current exploratory study compared the performance of 42 small tourism businesses operating in Serra da Estrela in an attempt to understand the impact of several factors on their success. Using occupancy rate as an indicator of success, a linear model was estimated, revealing the importance of adopting information and communications technologies (ICT) in tourism service as a factor for success. The study also shows that the supply of other services, besides housing, and client satisfaction promote the increase in net occupancy rates. Contrary to expectations, two of the explanatory variables related to management (owning and living in the touristic unit) have a negative impact on success.